Pentanal, 5,5-dimethoxy- → (E)-7-(4-chlorophenyl)-6-nitrohept-5-enal

HRID 1193019Notes

Reaction equation

HRID 1193019 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.C[O:14][CH:15](OC)[CH2:16][CH2:17][CH2:18][CH:19]=O>CCOC(C)=O.CCCCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]/[C:9](/[N+:10]([O-:12])=[O:11])=[CH:19]\[CH2:18][CH2:17][CH2:16][CH:15]=[O:14])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 170903Pentanal, 5,5-dimethoxy-HCID 114694951-(4-Chlorophenyl)-2-nitroethane

Product 1

HCID 25187598(E)-7-(4-chlorophenyl)-6-nitrohept-5-enalYield 45.1%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Prepared according to the general procedure B from 1-chloro-4-(2-nitroethyl)benzene 112g (24 mmol) and 5,5-dimethoxypentanal 131 (16 mmol) to provide the title compound as yellow oil (1.93 g, 45% yield) after silica gel chromatography (EtOAc/Hexane).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-2115f4463445473aac43aa1448f0dd0b
Source dataset
uspto-grants-2014_03
Patent number
US08680335B2

Reaction notes

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